


4 Times Being the Brother of the Anti-Christ Sucked (and how good that fifth time was.)

by hunters_retreat



Category: Supernatural
Genre: 5 Times, Anti-Christ!Sam, Demon!Dean, Fallen Angel Castiel, M/M, PWP
Language: English
Status: Completed
Published: 2015-12-03
Updated: 2015-12-03
Packaged: 2018-05-04 15:47:02
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,183
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5339678
Author URL: https://archiveofourown.org/users/hunters_retreat/pseuds/hunters_retreat
Summary: <blockquote class="userstuff">
              <p>The title says it all :P</p>
            </blockquote>





	4 Times Being the Brother of the Anti-Christ Sucked (and how good that fifth time was.)

 

 

1)      Personal (or Possession)

It doesn’t get more personal than this.  When Sam finally turns under the pressure of his blood, the ever increasing dangers that the dark side send against him, and the fear of losing his brother, everything goes to hell.  Literally.  The seals are all broken and hell on earth isn’t just a saying anymore.  Dean gets his ass thrown back into hell, but with Sam as the Anti-Christ, it’s not got the horror connected to it like it did the first time.  The problem is that topside, everyone is gunning for Dean.  They want to use Dean to get to Sam, help bring him out and into their traps, or to get Dean back to their side again.  Only they don’t understand that while Dean would have given anything to keep Sam from sliding into something he never wanted to be, Dean had learned for 10 years that Hell was almost where he belonged.  When Sam went, it was the only place he belonged.

 

 

She grunts under him, her eyes looking up over the table she’s bent over, watching him through the mirror.  He pushs up into her again, feels the soft slip slide of flesh and leans forward, pressing her bound hands harder into the table top.  Her struggles have left her wrists bloody and slippery but she can’t get away from him anymore.  He let his lips travel just behind her ear and whispered “You should have listened.”

 

 

He feels the press of another body, feels his brother behind him and he moans as pleasure rolls through his body, rocking with his cock inside Jo and Sam’s in him.  Sam slams hard into him, pushing him forward.  He hears Jo’s groan as her are forced harder into the table.  “Jo, you should have learned by now that you can’t take Dean from me.”  Both sets of eyes looked up in the mirror, staring at the white eyes that stared back at them, shivering.  Dean shivers in passion.  Jo shivers from fear. 

 

 

2)      Finances (or Magic Fingers)

Dean is lying in the bed and he really wants the magic fingers, only it’s been a while since he needed to carry money on him.  It seems sort of wrong to send one of the demons out to find him some quarters.  When Sam comes back to their room he looked at Dean on the bed, sees his expressive pout, and falls into the bed laughing.  “Pleasure button!”

 

 

Dean pouts more, but it doesn’t last long.  It turns out Dean does have a pleasure button and Sam has magic fingers all his own.   

 

 

3)      Friends (or How Sam found Dean new friends)

As the new demon on the block, Dean is a little on the ‘fresh meat’ side of things.  With 3 notable exceptions.  1) He’s Sam’s big brother and anyone trying to carve something out of him will find it carved out of themselves tenfold should Sam find out.  2) Dean is not new to hell, he has in fact lived there for 40 years before he moved out and the demon hierarchy can’t seem to figure out if that means he get his seniority back or not.  3) Dean was a carving boy and while demons are terrified of Aleister, they are still afraid of the non-demon all too human soul who he said ‘had potential’ before he’d ever gone black eyed.

 

 

Dean doesn’t know what to do about it.  He hates people thinking he can’t take care of himself, that he needs Sam to make him strong in other’s eyes.  In the end he decides points 2 and 3 are workable and when his birthday comes around, he asks Sam for two things.  1) Ruby’s knife and 2) Aleister. 

 

 

Sam gives him both and takes a couple days to watch Dean as he straps Aleister down and gets to work.  He talks to Sam like he wants to show him everything he’d learned in those first 10 years and Sam thinks quietly that Dean would have been an awesome teacher.  Hell, he still could be.  Aleister’s position will probably be vacant.  He smiles warmly at Dean, throws Aleister off the makeshift table, making a mental note to get his brother some proper equipment, and fucks Dean using Aleister’s blood to slick the way.  They fuck rough against the bloodied surface and when they’re done there’s very little pale skin showing through the blood stains. 

 

 

Sam licks Dean’s neck afterwards and wrinkles his nose.  “Dude, you taste like Aleister.  We need a shower.”

 

 

Dean laughs, then looks down at Aleister.  “Be good now.  I’ll be back to finish later.”

 

 

Aleister watched them walk away and sobs into the leather strap that covers his mouth.  Dean looks back, sees it, and smirks.  Being a newbie is probably not a problem anymore.

 

 

 

 

4)      Impala (or Death to stupid demons)

Dean is barely topside when someone decides that the best way to rise in the demon ranks is to get rid of Dean and the best way to do it is to do something to his car.  They’re obviously thinking some sort of demon homicidal rage that will have the other’s at arms and demanding his head on a platter. 

 

 

The thing about demons is that they never understood the Winchester boys as well as they thought.

 

 

The Impala gets beat all to hell in an accident, while Dean is in it no less.  Dean goes into the homicidal rage and demands that Sam hand over whoever did it.  Sam makes sure his brother is alright, then looks to the demons he keeps close and asks for a name.   There is no admission of guilt, but the others all look back at one of the newer members of their group, his body not that dissimilar to Dean’s though the eyes were all wrong and even if Sam were inclined to close his eyes and pretend the eyes would never work for him. 

 

 

Sam just smiles at him.  So does Dean.  When Dean puts him on the rack, the demon sobs for days, begging for forgiveness while Sam goes into long drawn out stories about their childhood, the road, and how the Impala, with Dean driving it, was the only home he ever had. 

 

 

The demon never quite recovers.  He doesn’t speak for years and when he does it’s only one word.  “Impala.”  With such a tone of fear and respect and pain and longing that everyone leaves the poor bastard alone.  Demons look away from the black car after that for fear of Dean’s wrath and the knowledge that Sam would do anything to placate Dean over her. 

 

 

 

 

 

 

5)      Angels (or Dean Winchester’s Cock is forbidden fruit)

Sam finds a way to bind Castiel and puts him in chains.  Sam wants to watch an angel fall and he’s convince that Dean is the one to do it.  When Sam sets himself a home base, Castiel’s chains are tied to the end of Dean’s bed.  They don’t torture him, just make him sit at the end of the bed, watching.  He can feel Castiel’s eyes on him; feel the heat of his gaze riding his body as he rides Sam.  Castiel moves closer, those angel eyes as incomprehensible to Dean as they had been when he was still human.  Castiel grows more and more curious and the curiosity often takes the form of disgust later, but he doesn’t seem to be able to stop himself from crawling on all fours, pale flesh contrasting with the shadow wings he can see so clearly now.  He stops across from Sam and Dean, his eyes drinking in the sight of the brothers.  Dean reaches his hand out and touched Castiel’s head, his fingers wrapping around hair and pulling slightly.  Castiel looks up, eyes dark with something he’s never understood but obviously wants.  “Say it.”  Dean demands and his voice is like honey dipped in sin so sweet it’s forbidden fruit. 

 

 

Sam’s hips piston up into him and Dean lets his head fall back, his fingers staying in Castiel’s hair.  He wants it as bad as Castiel, wants Castiel under him with Sam over him and thrusting into virgin flesh. 

 

 

“Ask me.”  Sam holds his hips still, pulling Dean off his lap and onto his stomach on the bed, his face bare inches from Castiel’s.  He slides back into Dean’s body and Dean arches into it.  “Come on Cas, want to feel you, want to ride into your body and make you feel it.”

 

 

Castiel looks like surrender, his eyes wide and watching, his lips slicked from wetting his lips.  Sam takes it as the ultimate moment and moves again.  He’s resting on his heels with Dean’s back pulled tight to Sam’s chest as he rests on Sam’s thighs.  Dean’s facing Castiel and the angel can’t keep his eyes off of Dean’s naked form as Sam thrusts up into him, Dean’s head thrown back onto Sam’s shoulder.  Sam watches Castiel, watches the way he looks at Dean and smiles.

 

 

“Tastes so fucking good Cas.  Like all the things He made and never let you have.  Like freedom and independence. Free will.”

 

 

“What would you know about it?”  Castiel asks.

 

 

Sam’s smile turned bitter.  “I had a father too.”

 

 

Castiel’s eyes turn from Sam’s and he knows that the angel doesn’t like the empathy.  Anti-Christ he might be, but his empathy has always been one of his strengths.  It works as well understanding your enemy as securing allies. 

 

 

Castiel’s eyes return though, unable to stop it. 

 

 

“Sam… please…” Dean’s begging for release and Sam won’t touch him. 

 

 

He nips at Dean’s sensitive ear.  “Ask him Dean.”

 

 

Dean looks down at Castiel then, eyes heavily lidded and lashes moving slowly in languid anguish as Sam tortures him without release.  “Cas… want you… need you… touch me Castiel.”  His voice is clear suddenly, commanding and certain that Castiel will do what he wants.  “Want you to wrap those lips of yours around my cock until I come down your throat.”  He thrusts his hips forward in time with one of Sam’s thrusts and sees Castiel lick his lips again.  His eyes close briefly and Dean lets out a breathy moan when Sam reaches around and begins playing with one of his nipples.

 

 

Dean doesn’t see Castiel move, but Sam does.  Sees the moment the angel falls, with his wrists still bound in chains, he pulls against them bringing one hand up to Dean’s cock as his tongue licks the tip, pre-come lapped up like a good little dog.  Dean almost comes apart from that alone but then Castiel opens up his mouth and takes him in.  Sam tightens his grip on Dean’s hips, riding him up into Castiel’s mouth.  The angel is moaning almost as much as Sam and Dean.  Dean’s eyes are open then, open and watching his dick disappear into Castiel’s mouth and then his whole body goes stiff.  Castiel keeps sucking, his lips sliding up and down Dean’s length and he can see in Castiel’s face the moment Dean comes, feels it in his body at the same time.  He doesn’t last as his eyes focus on the angel’s throat swallowing down his brother’s come. 

 

 

When he moves away from his brother, Sam climbs to the end of the bed and removes the chains.  Dean is lying on the bed looking up at the ceiling and trying to catch his breath. The night is far from over even if Castiel doesn’t know it yet.  Sam pulls Castiel off his knees and he’s guided easily onto the bed next to Dean.  Sam lies on the other side of Castiel, keeping their tamed angel in their collective embrace.  Dean leans up onto one arm and lets one hand trace circles into Castiel’s stomach, unable to stop from touching all that pale flesh. 

 

 

Sam leans down to kiss Castiel, demanding entrance to his mouth so he can taste his brother there.  “Not such a bad way to fall, huh Cas?”

 

 

The other man’s answer is a moan as Dean’s hand closed around his cock.  “Thing is I’ve been following Dean around my whole life.  When we were killing demons, I never met a one of them that didn’t get wet with him in the room.  Oh, they wanted to kill him, but they wanted to fuck him first.  Never met a challenge he couldn’t conquer.  God made Dean Winchester irresistible, even for  baby brothers.”  He said, looking up and smiling at Dean.  The smile was warmth and love and something that Castiel craved more than anything else.  When Sam looked back at him, there was warmth for him too, and heat.  “Apparently for angels too.”

 

 

Dean leaned in, his eyes sparkling.  “I couldn’t turn my back on Sammy, just like I knew you couldn’t turn your back on me.”

 

 

He kissed Castiel, then reach a hand out to Sam, who reached over Castiel’s body, Dean’s hand still working his cock, and kissed him.  When Dean slid down Castiel’s body, Sam cupped Castiel’s face and smiled.  “Welcome to the family."

 

 


End file.
